


To Have and Have Not

by darkandtwisty



Category: Supernatural
Genre: Age Difference, Alcoholic Dean, Dean x You - Freeform, Dean's got it bad, Domestic Dean, Domestic Dean Winchester, Drinking, Eventual Smut, Ex-Military Dean, F/M, Flirting, Flirty Dean, Fluff, Insecurity, Mentions of Death, No Underage Sex, Older Man/Younger Woman, Reader-Insert, Reader-Interactive, Sarcasm, Self Confidence Issues, Self-Loathing, Series, She's not underage, Soldier Dean, Soldier Dean Winchester, insecure reader, sarcastic reader
Language: English
Status: In-Progress
Published: 2016-05-04
Updated: 2016-05-04
Packaged: 2018-06-06 10:37:03
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,593
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6750475
Author URL: https://archiveofourown.org/users/darkandtwisty/pseuds/darkandtwisty
Summary: <blockquote class="userstuff">
              <p>A look into your life with Dean throughout the years. Starting when you meet him at the bar you work at, when he isn’t having the best night. There's some strange connection between you and the ex-soldier and you bond over the fact that you both have your fair share of problems.</p>
            </blockquote>





	To Have and Have Not

**Author's Note:**

> Listen to Falling Slowly by Glen Hansard while you read! 
> 
> M rating for future smut.

**November 2, 2010**

A shiver wracked your body; the cold nighttime air biting at your cheeks as you stepped out of the bar. You reached into your purse, grabbing your cigarette pack and searching for your lighter. A groan leaves your lips when you realize it’s not there. You squint, trying to see; the only light being the glow from the bar’s sign overhead.

 _The Hitching Post_ , it read in big blue letters.

“Anybody got a match?” You asked to no one in particular, glancing around and making eye contact with the few people standing, scattered across the sidewalk.

The people standing around you all shook their heads and resumed mingling amongst themselves.

Someone cleared their throat behind you, “Hey kid, you know how bad that shit is for you right?” The husky voice asked. He had that “to much whiskey” voice and it was pure sex.

You turned to face the stranger behind you, only to be met with the gaze of the most attractive man you had ever seen. It was the same guy that you had seen sitting at the far right end of the bar all night. He was standing there smirking at you in a long dark coat, hands in his pockets; his breath visible and blowing out in puffs in front of his face. He took a few steps forward until he was standing next to you, your shoulders almost brushing.

“Bad habit,” You chuckled, “Only when I’m stressed,” You shrugged, “I’m assuming you don’t have a match or a lighter, do you?”

“I do but, I’d really rather not add to your bad habit, if you don’t mind.”

You scoffed, looking at him in disbelief.

“Usually when I think the bartender is cute, I ask for her number, not contribute to her getting cancer.” He shrugged, eyes trailing up and down your frame.

_Did he just call you cute? Was he blind?_

You shifted under his heavy gaze, insecurity washing over you. You shoved the feeling down and smiled shyly.

Dean had his eye on you all night. He didn’t think he had ever seen a more beautiful girl in his life. He hadn’t intended on speaking to you. You were obviously much younger than him and the last thing he needed to do was start something he couldn’t finish, but something drew him to you.

“Speaking of bad habits, I saw you in there throwing back whiskey shots like someone just broke your heart.”

“Looks like we both have unhealthy ways of relieving stress.”

You cleared your throat, “Technically, I was contributing to your bad habit, then.”

“Not really, considering you never made your way down to my end of the bar.”

A smile slowly made its way across your face. Truthfully, you saw him glance your way earlier that night, but it was brief and you hadn’t thought much of it. Though you would be lying if you said you didn’t feel some anomalous connection- like something was pulling you towards him.

“Pretty daring, drinking like that considering this is the hunting ground for all the cougars. They prey on tipsy, handsome men like yourself.” Where you… _flirting_ right now? Was this flirting? Because you didn’t usually flirt; you were relatively quiet and semi-awkward when it came to men. Especially men as good looking as the scruffy, intimidatingly tall one standing next to you. Without the tiny bit of liquid courage you had coursing through your system, you doubt you’d had even looked in the guys direction. You had avoided his gaze in the bar earlier.

 

“What can I say? I’m brave.” He beamed, showing off a beautiful smile that sent butterflies loose in your stomach, as his eyes studied your face.  
This guy was charming, and a tad cocky, you kind of liked it. He was arguably the most attractive man you had ever encountered. You’d never met anyone so alluring. It was kind of intimidating.

You were gonna go out on a limb here and say that maybe this guy kind of liked you, just by the way he was looking at you; no one had ever looked at you that way before. Hell, maybe he did.

That little voice in the back of your head was telling you to do something before this guy walks away and you never see him again. You decided to take a step outside of your comfort zone and before you could stop yourself you were asking him to have a drink with you. “Why don’t you let me buy you a drink and you can tell me why you got so much stress to relieve?”

“Sweetheart, I would love to but-,” The dejected look on your face made him feel instantly guilty. He could tell that wasn’t something you did often, or ever. He knew he shouldn’t but God did he want to. He was internally fighting with himself. He knew it was a bad idea but he didn’t want to risk you leaving and him never seeing you again. He knew you were beautiful before but you now standing here talking to you, he was at a loss for words. You were mesmerizing; and he wanted to know more about you. He wanted more. The alcohol clouding his judgment ultimately swayed his decision. “You know what, I’ll take you up on that drink on one condition, let’s sit outside.”

—–

The handsome stranger, who you learned was named Dean, and you, sat at one of the small metal tables in the gated outdoor area of the bar. You were the only two sitting outside, other than a group of young women chatting in the corner.

“So, what’s got you so stressed that you’re damn near drinking yourself into coma on a Monday night?”

“I’m not exactly a lightweight, doll.” He laughed once, his expression quickly turning serious. Dean’s eyes drifted down, focusing intensely on the patterns etched into the metal. 

“Today is the uh- anniversary of my mom’s death.”

“Oh god, I shouldn’t have-”

“No, don’t- you’re fine, really.” He cracked a small smile and placed his hand over yours on the table.

You sighed, “I’m sorry, Dean.” you placed your free hand on top of his, that was still covering yours. “How about that drink?” You asked, and the corners of his mouth quirked up slightly.

You returned to the table with a beer for each of you. “Do you wanna talk about it?”

He shrugged, taking a pull from his bottle. You could tell he was trying not to look as broken up as he probably was. 

The last thing he wanted was for you to pity him.

You leaned closer to him across the table, “Why don’t you tell me about her?”

His eyes shot up to meet yours and he looked surprised. A big smile worked it’s way onto his face and he squinted at you briefly before leaning towards you and nodding slowly.

The concern and care in your tone caught Dean by surprised. He had expected the usual, “I’m sorry for your loss” blah blah blah. He hadn’t talked about his mom with anyone in years, but for some odd reason, he wanted to tell you about her.

_And you wanted to hear._

You got lost in conversation. He told you about his mom, and how she died in a house fire when he was young. His face lit up as he spoke about her. He showed you the picture of the two of them that he kept in his wallet; she was beautiful and he had her eyes. Those beautiful green eyes that you got lost in as he talked. 

He talked about his classic car that he loved so much and his younger brother Sam, who studied law at Stanford. Sam was a lawyer and lived in California with his girlfriend Jessica. He spoke about him with such pride. From what you gathered, Sam seemed to be the most important person in Dean’s life and it was obviously hard on him having Sam live so far away. All he had in Kansas, since his Dad passed away a few years ago, were a few friends that he considered family, and an Uncle.

He told you about how he enlisted when he was 18, and about the time he spent in Afghanistan. How he was released from his obligation to serve at 28 due to a back injury that almost left him paralyzed. Now he was a mechanic at Singer’s Automotive over on 6th Street. The body shop was owned by the last bit of family he had; his Uncle Bobby who incidentally was married to Jody Mills; the owner of The Hitching Post.

“I know they call it honorable discharge, but there ain’t nothing honorable about what happened to me.” He had told you.  
The shame was evident in his voice. Dean believed it was entirely his fault; that he was too weak to “keep grinding” as he called it. You had this overwhelming urge convince him otherwise; something you made a mental note to do, given the opportunity later.

Anxiety fled through you when he turned the attention off of him, wanting to know more about you. So you stuck to the basics. You told him about your mom, who you had just lost a few months ago, and your dad who you didn’t have the best relationship with. Then there was your best friend, Meg and your little sister Ruby. He asked about you working at the bar, and you told him how you only took the job because it was the easiest way to pay the bills while you were still in college.

Talking to Dean felt so easy, natural, like you had known each other for years. Sure you had butterflies in your stomach and your body was thrumming with excited and underlying lust, but you weren’t the blushing, fumbling mess you would usually be. All that latent insecurity wasn’t at the forefront of your mind, and damn if it wasn’t nice.

—–

“-jumped off the shed! He was convinced we were superheroes; poor kid broke his arm. I had to rush him to the hospital on the handlebars of my bike.” Dean’s uninhibited laughter filled the air as he recounted one of his favorite memories with his brother.

His smile was bright and you had tears in your eyes as you wheezed with laughter right along with him.

You wiped a tear from your eye, “Oh that sounds like the worst kind of reality check.”

“Hey, nobody said I wasn’t Batman!” He defended, making you giggle and roll your eyes.

Dean watched you as you laughed, head thrown back, nose scrunched up in the cutest way and all he could think was, _God, who is this girl?_

He felt so drawn to you, so taken with the way you didn’t take his shit and listened to him talk about his screwed up past without a hint of judgment in your eyes. For the first time in a long time, he had a real conversation with someone who he felt like, understood him. Someone he had just met, yet felt such a strange connection with. He couldn’t help but feel guilty, for allowing himself the luxury of starting something he knows he shouldn’t. You were young and beautiful and sweet. He wouldn’t be the one to ruin that. I mean, sure, you had your own problems too but they were minuscule compared to his. He was too damaged. Yet, here he was, sticking his neck out.

“I shouldn’t even be sitting here with you. We’re playin’ with fire here.”

“And why is that?” You asked with a sigh.

“Because you’re so young, I mean god, you’ve got to be what- 24, 25?”

“22.”

“Damn, you’re just a baby aren’t you, doll?”

You could feel the heat slowly rise to your cheeks, “Then why are you sitting here with me?”

“Felt like I’d be makin’ a mistake if I didn’t.”

_Whoa._

“And what’s so bad about you huh?”

Dean scoffed, “I’m not all good and pure, kid. I’ve got some darkness in me. You didn’t pick that up from everything I told you?”

“No, you’ve seen and been through some shit. Haven’t we all? Who says I’m good and pure? Maybe I have a little bit of darkness in me too.”

“I got a lot of darkness in me, sweetheart. You don’t want to deal with all that baggage.”

“You wanna talk about baggage? I got a mountain of that. Y'know, the daddy issues and self-loathing; the classics. ”

 

“I mean, I knew you were a little messed up, otherwise you wouldn’t be sitting here talking to me.”

“Oh, you have no idea.”

Dean looked amused. “Enlighten me, then.”

“That’s a story for another time, old man.” You say the last part sarcastically.

“That’s a story I wanna hear.”

You nodded, “So, maybe we’re both fifty shades of fucked up.”

“I’ll drink to that.” He laughed as raised his beer bottle proudly to clink against yours.

—–

“10 years apart, so what? That’s nothing, at least not to me.”

“You’re too young, I’m too old. Why would a beautiful young thing like yourself, want an old man like me?”

“Oh please, Dean. You aren’t old. Why wouldn’t I?” You pulled your plush bottom lip between your teeth absentmindedly, your eyes studying all his features. The action causing 

Dean to twitch in his jeans. _What in the hell were you doing to him?_

A toothy grin spread across Dean’s face and he leaned towards you across the metal table. He was so close you could feel his breath fanning across your face.

“You’re trouble.” He affirmed, pointing a finger at you.

_Goddamn, this boy is addicting._

You shrugged, “Maybe, but hey, you said you were brave.”

Dean bit his lip, slowly shaking his head in disbelief as he ogled the oddly enchanting, young girl in front of him. He wasn’t sure what it was but something about you had his stomach doing back flips. Never in his life, had Dean felt this way about a woman, let alone one he had just met outside a bar in the freezing cold. You were a stranger but it sure as hell didn’t feel like it. He didn’t know what it was but he wanted to get to know you; wanted to learn every small detail about you that had yet to be uncovered by anyone else. He was definitely older than you were and he tried not to let the thought that maybe he could have you in ways no one ever has before, stir up something possessive in him.

Your soft, curious voice broke him of his reverie, “What do you want, Dean?”

“A whole lot of things I can’t have.”

“As in?” You pressed.

“Sammy to live here in Lawrence, my mom back, you. I mean, if circumstances were different, maybe I’d get your number, take you out on a date. Wine and dine you.” He chuckled to himself.

_Please._

“And why can’t you?”

“I already told you.”

_This boy is infuriating. Why did he have to think so low of himself?_

“You told me a bunch of bullshit that I’m not buying into. Stop trying to find an excuse to keep yourself from being happy, or having something you want.” You said it like it was the most obvious thing in the world, and it threw Dean for a loop. “You seem like you’ve been at war with yourself for long enough. Don’t you think it’s time that you won?”

“Who are you?” He whispered, mostly to himself. You not taking Dean’s shit, was incredibly sexy. Maybe that’s what he needed; someone to call him on his shit. _Fuck, why did you have to be so perfect?_

You smiled brightly, “Tonight? I don’t know.”

There was something captivating about the handsome, enigmatic, older man sitting with you. He was funny, sarcastic and…sexy and you wanted to take him home with you. However, he was a stranger, although it sure as hell didn’t feel like it. It was strange and terrifying but wildly exciting.

—–

You and Dean had sat at that small metal table and stayed deep in conversation until you heard them yell last call from inside.

“Damn, is it really 3am?” You asked, running a hand through your hair.

“Yeah, I-I uh guess it is.” He chuckled, shyly.

“I should probably get home.”

“Yeah, me too. But uh, hey before you go-.” He paused to reach into his pocket, pulling out a small matchbox.

“Oh, now you’ll give me a match.”

He chuckled, “Because, you can give me something in return.”

“What’s that?”

“Write your number on the back?” He asks, a hopeful grin on his face, matchbox in hand. When your brows furrow and curiosity is written clear across your face, he adds, “Taking your advice. Letting myself have something I want.”

“And just why in the hell would you want _my_ number?”

“Besides the fact that you’re beautiful, smart, and you’ve made me laugh more in the past couple hours than I have in months?” He questions, eyebrows pinched together, and chewing on his lip. You blush and shake your head in disbelief as he smiles at you. “Beats the hell outta me kid, but I feel like if I don’t… I’m really gonna regret it in the morning.”

“Or maybe it’s just the alcohol talking.” You suggested, swirling your finger around the edge of your empty beer bottle.

You grabbed the withered matchbox that is being pinched between his pointer fingers and held in your direction. You turned it around and there on the back, is a name written messily in black sharpie.

You study the small cardboard box as you grab your purse and rise from your seat. Dean followed you as you walked slowly to the edge of the curb. “Dean Winchester.” You murmur mostly to yourself.

He hummed, “Would’ve told ya’ my full name but damn, it sounds much better coming out of your mouth.” He utters, voice dropping a few octaves, making you shiver.

“You’re flirty when you get what you want, Winchester.” You tease, smirking at him.

“You have no idea, baby.”

_Stop making me blush, you ass._

You lay the small box in the palm of your hand, pulling a pen out of your purse before scribbling down your phone number and placing it in his awaiting palm.

Dean tucked the box back into his coat pocket and smiled at you, his eyes flickering back and forth between your eyes and lips.

_That’s it._

In a moment of insane courage, you lean forward, standing on your tippy toes just enough to brush your cold lips against Dean’s. His lips molded to yours passionately, letting out all that built up need. His pointer fingers slid into your belt loops and dragged you impossibly closer.

When you pulled away Dean was grinning wildly and you could feel the heat radiating off your cheeks.

“What did you do that for?” He whispered, eyes droopy and looking sated.

“Figured I would let myself have something that _I_ want, and I wanted to see if I’d like it.”

“What’s the verdict?”

“I think I’d like your help next time.” You whispered, reaching up to push your fingers through his hair.

His eyes were fixed your lips and then he’s grabbing your hips and pulling you to him; crashing your lips together, rougher this time. One hand cupped your jaw while the other slid up to fist in your hair. You tugged on the material of his dress shirt, pulling his body flush against yours. Normally, PDA wasn’t your thing, but Dean was standing there looking at you like he wanted to devour you, and you were just supposed to resist that? No way in hell.

After a few minutes you broke the kiss to get a proper breath of air.

 _Let me take you home_ , was the only thought running through Dean mind.

You giggled, and Dean realized his internal monologue wasn’t so internal.

_Lord knows you wanted to let him._

He goes to lean back in, his eyes still heavily focused on your lips but you stop him, placing a hand on the thick lapel of his coat.

You smiled up at him, “Call me when you’re sober, Winchester.”

He placed his palm over the hand resting on his chest and squeezed slightly, stroking your fingers with his thumb, “Oh, you can expect a call from me, doll.”

You start to pull away but he tugs you back to sneak a quick kiss on your cheek, turning your them rosy once more.

He releases you, and you walk away backwards, still facing him. “Talk to you then.” You whisper, turning around.

Dean watched you walk away, fighting the urge to run to you and convince you to come home with him. He was definitely going to see you again, if he had any say in it.

“Wait!” He yelled causing you to turn around, “I just realized, all that and I didn’t get your name.”

You giggled as you shouted, “Y/N. Y/N Y/L/N.”

“It was nice to meet you, Y/N Y/LN.”

“It was nice to meet you, Dean Winchester.”

You turned around, starting to walk away before he was calling for you again.

“Hey kid, wait up.” He said, jogging after you. 

“Yeah?”

“Let me walk you home?”

“Don’t wanna say goodbye yet?”

He grinned, “Not in the slightest.”

Truth is, you didn’t either.

**Author's Note:**

> I am SO excited about this one. So, I was reading about Humphrey Bogart and Lauren Bacall’s incredible love story and I fell so in love with those two. Then this idea popped into my head and I just HAD to write it. This is very, very loosely based on them. Mostly I just drew inspiration from their relationship. We are gonna jump around throughout the years so each chapter is going to be a different time-stamp. I know the POV is a little confusing since you see inside both yours and Dean’s head. Let me know if you want part 2!
> 
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> 
> deanscherrypie.tumblr.com


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